is probably the easiest to get into, and if you heard bits of the recent stuff and like the sound of it that is probably where to start. Black Sheep Boy is the best album, though, and the earlier albums have some real standouts (eg Maine Island Lovers, my favourite OR song)without being as consistantly good. Actually fuck it, just get everything they've done and listen to it, it's all pretty fantastic. Hope that helps. Oh, and an easily overlooked non-album song of theirs that is a shoo-in for any Okkervil top 5 tunes list can be heard here:

it flows together beautifully, the dynamics across the tracks work so well, and the whole thing just has such a consistent sense of atmosphere. lovely production too
see also: black sheep boy appendix, to a slightly lesser extent

the others all have some incredible songs but none of them have ever really clicked for me as a whole in the same way

It depends what you like? It seems now the okkervil river fan club is divided into two camps...

1. People who prefer the first two albums (Don't Fall In Love With Everyone You See and Down The River of Golden Dreams) and i think this is one band, where the people who say this are not the usual 'cool kids' saying they prefer the early stuff to look good. Its because these are the more folky storytelling albums, mandolin-and-banjo-a-plenty. And in my opinion Will Sheff at his artistic best. Still blessed with youthful naivety and not yet filled with any goal to achieve anything other than a song he would like to listen to himself. The ideas of mass appeal or large crowds are still something he has never thought about (not saying that in a derogatory sense). I feel if you get into these albums, you will be a fan for life, whereas with the more recent ones, there isnt enough to keep you in and really enthrall you in the same way.

2. The people that prefer Black Sheep Boy, and more often than not, these people also prefer The Stage Names and The Stand In's over the first new albums. I feel this is because, Will wrote a few songs very atypical for them at that point on Black Sheep Boy, such as Black. This almost emo-pop-folk-rock (i dont know) thing, caused more people to pay attention than before, and this fact, which they were surely must have been aware off (be it subconsciously or not) resulted in some far rockier, poppier, upbeat albums of late.

Say whatever you want over me saying there is an element of calculation behind it, but thats not a bad thing, its just practice on the songwriters behalf, you learn what people pick up on, and try and produce more of that. Just like Conor Oberst, he freely admits that he is now a better songwriter than ever, and what does 'better' mean, surely it means the ability to write a song that appeals to as many people as possible. Thats very hard to do, and its not something to criticize people over, its something to commend. Any one can write a load of shit that some DiS readers will like, thats no skill. You only have to listen to the more recent Okkervil River lyrics, to realise that even Will knows how to play the game and what people want. No Key No Plan for example...."im back on the road again, with maybe 13 grand" "moralise all you may like" "doing what i really like and getting paid for it".

But anyway, I am a huge Okkervil River fan, and in my eyes, they can do no wrong, but I really do think, that the first two albums are a million times superior to the recent ones, but thats maybe looking back to the time when i discovered them albums, spending the summer with them playing full blast, and now, knowing them, its not exciting, maybe I would have had more fun with The Stage Names, if that was out then, you never know

Mainly because 'For Real' was the first song of theirs that I heard and it completely blew me away. Then, when I finally got the album and heard 'Stone' for the first time, that was it. They could do no wrong and I just had to have all the rest of their stuff. I have plenty of other favorites now, but that's how it all started.